Skip to main content
SpringerLink
Log in

Synthesis of Novel Benzofuran Based 1,2,3-Triazoles, Their Antimicrobial and Cytotoxic Activities, and Molecular Docking Studies

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

A series of novel {5-[(1H-1,2,3-triazol-4-yl)methoxy]-3-methylbenzofuran-2-yl}(phenyl)methanone derivatives has been synthesized with high yields, characterized by IR, NMR, and mass spectroscopy, and elemental analysis. According to their cytotoxicity tests, majority of the target compounds exhibit good activity against A-549 cells using Doxorubicin as the standard drug. The products demonstrate high antimicrobial activity. Molecular docking studies have been performed against 2XCT. Most of the compounds have been characterized by good binding interactions with the target.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1.
Fig. 1.

Similar content being viewed by others

REFERENCES

  1. Sunitha, V., Kishore Kumar, A., Shankar, B., Anil Kumar, A., Krishna, T. M., Lincoln, C.A., and Pochampalli, J., Russ. J. Gen. Chem., 2017, vol. 87, no.2, p. 322. https://doi.org/10.1134/S1070363217020281

    Article  CAS  Google Scholar 

  2. Xie, Y.-S., Kumar, D., Bodduri, V. V., Tarani, P. S., Zhao, B.-X., Miao, J.-Y., Jang, K., and Shin, D.-S., Tetrahedron Lett., 2014, vol. 55, no. 17, p. 2796. https://doi.org/10.1016/j.tetlet.2014.02.116

    Article  CAS  Google Scholar 

  3. Rida, S.M., El-Hawash, S.A.M., Fahmy, H.T.Y., Hazzaa, A.A., and El-Meligy, M.M.M., Arch. Pharm. Res., 2006, vol. 29, no. 10, p. 826. https://doi.org/10.1007/BF02973901

    Article  CAS  PubMed  Google Scholar 

  4. Cottineau, B., Toto, P., Marot, C., Pipaud, A., and Chenault, J., Bioorganic Med. Chem. Lett., 2002, vol. 12, no. 16, p. 2105. https://doi.org/10.1016/S0960-894X(02)00380-3

    Article  CAS  Google Scholar 

  5. Thévenin, M., Thoret, S., Grellier, P., and Dubois, J., Bioorg. Med. Chem., 2013, vol. 21, no. 17, p. 4885. https://doi.org/10.1016/j.bmc.2013.07.002

    Article  CAS  PubMed  Google Scholar 

  6. Bazin, M.-A., Bodero, L., Tomasoni, C., Rousseau, B., Roussakis, C., and Marchand, P., Eur. J. Med. Chem., 2013, vol. 69, p. 823. https://doi.org/10.1016/j.ejmech.2013.09.013

    Article  CAS  PubMed  Google Scholar 

  7. Xie, F., Zhu, H., Zhang, H., Lang, Q., Tang, L., Huang, Q., and Yu, L., Eur. J. Med. Chem., 2015, vol. 89, p. 310. https://doi.org/10.1016/j.ejmech.2014.10.044

    Article  CAS  PubMed  Google Scholar 

  8. Oter, O., Ertekin, K., Kirilmis, C., Koca, M., and Ahmedzade, M., Sens. Actuators B: Chem., 2007, vol. 122, no. 2, p. 450. https://doi.org/10.1016/j.snb.2006.06.010

    Article  CAS  Google Scholar 

  9. Chand, K., Rajeshwari, Hiremathad, A., Singh, M., Santos, M.A., and Keri, R.S., Pharmacol. Rep., 2017, vol. 69, no. 2, p. 281. https://doi.org/10.1016/j.pharep.2016.11.007

    Article  CAS  PubMed  Google Scholar 

  10. Raghavender, M., Kumar, A.K., Sunitha, V., Vishnu, T., and Jalapathi, P., Russ. J. Gen. Chem., 2020, vol. 90, no. 4, p. 697. https://doi.org/10.1134/S1070363220040210

    Article  CAS  Google Scholar 

  11. Manikala, V.K. and Rao, V.M., Russ. J. Org. Chem., 2020, vol. 56, no. 5, p. 863. https://doi.org/10.1134/S1070428020050206

    Article  CAS  Google Scholar 

  12. Das, K., Bauman, J.D., Rim, A.S., Dharia, C., Clark, A.D.Jr., Camarasa, M.-J., Balzarini, J., and Arnold, E., J. Med. Chem., 2011, vol. 54, no. 8, p. 2727. https://doi.org/10.1021/jm101536x

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Angajala, K.K., Vianala, S., Macha, R., Raghavender, M., Thupurani, M.K., and Pathi, P., SpringerPlus, 2016, vol. 5, no. 1, p. 423. https://doi.org/10.1186/s40064-016-2052-5

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Holla, B.S., Mahalinga, M., Karthikeyan, M.S., Poojary, B., Akberali, P.M., and Kumari, N.S., Eur. J. Med. Chem., 2005, vol. 40, no. 11, p. 1173. https://doi.org/10.1016/j.ejmech.2005.02.013

    Article  CAS  PubMed  Google Scholar 

  15. Kumar, A. K., Sunitha, V., Shankaraiah, P., Siddhartha, M., and Jalapathi, P., Russ. J. Gen. Chem., 2018, vol. 88, no. 4, p. 789. https://doi.org/10.1134/S1070363218040254

    Article  Google Scholar 

  16. Kumar, A.K., Sunitha, V., Shankar, B., Krishna, T.M., Lincoln, C.A., and Jalapathi, P., Russ. J. Gen. Chem., 2017, vol. 87, no. 9, p. 2011. https://doi.org/10.1134/S1070363217090171

    Article  Google Scholar 

  17. Kumar, A.K., Sunitha, V., Ramesh, G., and Jeshma, K., Russ. J. Gen. Chem., 2021, vol. 91, no. 12, p. 2546. https://doi.org/10.1134/S1070363221120264

    Article  CAS  Google Scholar 

  18. Kumar, K., Pradines, B., Madamet, M., Amalvict, R., and Kumar, V., Eur. J. Med. Chem., 2014, vol. 86, p. 113. https://doi.org/10.1016/j.ejmech.2014.08.053

    Article  CAS  PubMed  Google Scholar 

  19. Patpi, S.R., Pulipati, L., Yogeeswari, P., Sriram, D., Jain, N., Sridhar, B., Murthy, R., Kalivendi, S.V., and Kantevari, S., J. Med. Chem., 2012, vol. 55, no. 8, p. 3911. https://doi.org/10.1021/jm300125e

    Article  CAS  PubMed  Google Scholar 

  20. Liang, Z., Xu, H., Tian, Y., Guo, M., Su, X., and Guo, C., Molecules, 2016, vol. 21, no. 6, p. 732. https://doi.org/10.3390/molecules21060732

    Article  CAS  PubMed Central  Google Scholar 

  21. Sunitha, V., Kumar, A.K., Shankaraiah, P., Jalapathi, P., and Lincoln, C.A., Russ. J. Gen. Chem., 2018, vol. 88, no. 7, p. 1515. https://doi.org/10.1134/S1070363218070265

    Article  CAS  Google Scholar 

  22. Kant, R., Kumar, D., Agarwal, D., Gupta, R.D., Tilak, R., Awasthi, S.K., and Agarwal, A., Eur. J. Med. Chem., 2016, vol. 113, p. 34. https://doi.org/10.1016/j.ejmech.2016.02.041

    Article  CAS  PubMed  Google Scholar 

  23. Bauer, A., Am. J. Clin. Pathol., 1966, vol. 45, p. 493. https://doi.org/10.1093/ajcp/45.4_ts.493

    Article  CAS  PubMed  Google Scholar 

  24. Bax, B.D., Chan, P.F., Eggleston, D.S., Fosberry, A., Gentry, D.R., Gorrec, F., Giordano, I., Hann, M.M., Hennessy, A., and Hibbs, M., Nature, 2010, vol. 466, no. 7309, p. 935. https://doi.org/10.1038/nature09197

    Article  PubMed  Google Scholar 

  25. Friesner, R.A., Banks, J.L., Murphy, R.B., Halgren, T.A., Klicic, J.J., Mainz, D.T., Repasky, M.P., Knoll, E.H., Shelley, M., and Perry, J.K., J. Med. Chem., 2004, vol. 47, no. 7, p. 1739. https://doi.org/10.1021/jm0306430

    Article  CAS  PubMed  Google Scholar 

  26. Schrodinger, L., The PyMOL Molecular Graphics System, 2012.

  27. Dalla Via, L., Gia, O., Chiarelotto, G., and Ferlin, M.G., Eur. J. Med. Chem., 2009, vol. 44, no. 7, p. 2854. https://doi.org/10.1016/j.ejmech.2008.12.011

    Article  CAS  PubMed  Google Scholar 

Download references

ACKNOWLEDGMENTS

VS thanks TSWREIS for support and thanks CFRD, Osmania University, Hyderabad, India for providing analytical support. AKK thanks to Principal, Vardhaman College of Engineering, Hyderabad, Telangana, India for support. BSK thanks to Dr. Rama krishna Dumpati for providing docking support and SNIST, Hyderabad, Telangana.

Author information

Authors and Affiliations

  1. Telangana Social Welfare Residential Degree College for Women, Siddipet, Siddipet District, 506223, Telangana, India

    V. Sunitha

  2. Department of Humanities and Sciences, Vardhaman College of Engineering, Shamshabad, Hyderabad, 501218, Telangana, India

    A. Kishore Kumar

  3. Sreenidhi Institute of Science and Technology (Autonomous) Yamnampet, Ghatkesar, 501301, Hyderabad, India

    B. Saikrishna

Authors
  1. V. Sunitha
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. Kishore Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. B. Saikrishna
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. Sunitha.

Ethics declarations

No conflict of interest was declared by the authors.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sunitha, V., Kumar, A.K. & Saikrishna, B. Synthesis of Novel Benzofuran Based 1,2,3-Triazoles, Their Antimicrobial and Cytotoxic Activities, and Molecular Docking Studies. Russ J Gen Chem 92, 1348–1359 (2022). https://doi.org/10.1134/S1070363222070258

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363222070258

Keywords:

Search

Navigation